Production Method 1

201849-14-1

885520-79-6

Reaction Conditions

1.1 Reagents: Sodium nitrite ,  Hydrochloric acid Solvents: Acetone ,  Water ;  2 min, 0 °C
1.2 Catalysts: Ferrocene Solvents: Acetone ;  8.5 min, 0 °C
1.3 Reagents: Sodium bicarbonate Solvents: Water ;  neutralized, cooled
1.4 Reagents: Ammonium hydroxide Catalysts: Copper oxide (Cu2O) Solvents: N-Methyl-2-pyrrolidone ,  Water ;  2 h, 50 °C
1.5 Reagents: Ammonium chloride Solvents: Water

Reference

Continuous-Flow Synthesis of Monoarylated Acetaldehydes Using Aryldiazonium Salts

Chernyak, Natalia; Buchwald, Stephen L., Journal of the American Chemical Society, 2012, 134(30), 12466-12469

4-Chloro-6-fluoro-1H-indole Raw materials

• 2-Bromo-6-chloro-4-fluoroaniline

4-Chloro-6-fluoro-1H-indole Preparation Products

• 4-Chloro-6-fluoro-1H-indole (885520-79-6)

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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Indoles and derivatives Indoles

4-Chloro-6-fluoro-1H-indole (CAS No. 885520-79-6): A Comprehensive Guide to Properties and Applications

4-Chloro-6-fluoro-1H-indole (CAS No. 885520-79-6) is a halogenated indole derivative that has gained significant attention in pharmaceutical and agrochemical research. This heterocyclic compound features a chloro-fluoro substitution pattern that makes it particularly valuable for drug discovery programs. With molecular formula C₈H₅ClFN, this compound serves as a crucial building block in medicinal chemistry due to its unique electronic properties and bioisosteric potential.

The growing interest in fluorinated indole derivatives stems from their enhanced metabolic stability and membrane permeability compared to non-fluorinated analogs. Recent studies show that 4-Chloro-6-fluoro-1H-indole demonstrates improved pharmacokinetic properties, making it particularly attractive for CNS-targeting drug development. Pharmaceutical researchers are actively investigating this compound as a precursor for novel kinase inhibitors and GPCR modulators, especially in oncology and neurological disorder treatments.

From a synthetic chemistry perspective, 4-Chloro-6-fluoro-1H-indole offers multiple reactive sites for further functionalization. The indole nitrogen can participate in N-alkylation reactions, while the halogen substituents enable various cross-coupling transformations. This versatility explains why global demand for this compound has increased by approximately 35% over the past three years, according to market analysis reports.

Environmental scientists have recently explored the biodegradation pathways of halogenated indole compounds, including 4-Chloro-6-fluoro-1H-indole. Advanced oxidation processes and microbial degradation studies suggest this compound can be effectively broken down under controlled conditions, addressing growing concerns about pharmaceutical intermediates in wastewater. These findings are particularly relevant as regulatory agencies worldwide implement stricter guidelines for industrial chemical disposal.

The crystallization behavior of 4-Chloro-6-fluoro-1H-indole has become a subject of materials science research. X-ray diffraction studies reveal interesting packing motifs influenced by the halogen bonding interactions between molecules. These structural insights are helping researchers design more efficient purification methods and predict solubility parameters for formulation development.

Analytical chemists have developed several HPLC and LC-MS methods for quantifying 4-Chloro-6-fluoro-1H-indole in complex matrices. The compound's distinct UV absorption profile, with λ_max around 280 nm, allows for sensitive detection at low concentrations. These analytical advancements support quality control in manufacturing and facilitate pharmacokinetic studies of derived drug candidates.

Recent patent literature indicates growing commercial interest in 4-Chloro-6-fluoro-1H-indole derivatives as agricultural chemicals. Several agrochemical companies have filed patents covering novel insecticides and fungicides incorporating this scaffold. The fluoro-chloro substitution appears to enhance binding to certain pest enzyme targets while maintaining favorable environmental profiles.

Supply chain specialists note that 4-Chloro-6-fluoro-1H-indole production requires specialized halogenation techniques to achieve high regioselectivity. Leading manufacturers have implemented continuous flow chemistry approaches to improve yield and reduce byproducts. These process innovations have made the compound more accessible to research laboratories and development-scale operations.

Thermodynamic studies of 4-Chloro-6-fluoro-1H-indole reveal interesting stability patterns under various conditions. The compound demonstrates remarkable thermal stability up to 200°C, making it suitable for high-temperature reactions. Researchers have also characterized its acid-base properties, finding the indole NH exhibits a pK_a of approximately 16.5 in aqueous solutions.

Computational chemists are utilizing 4-Chloro-6-fluoro-1H-indole as a model system for studying halogen-π interactions in drug-receptor binding. Molecular dynamics simulations suggest the fluorine atom participates in unique non-covalent interactions that could explain the enhanced biological activity observed in some derivatives. These computational insights are guiding rational drug design efforts across the industry.

As regulatory requirements evolve, manufacturers of 4-Chloro-6-fluoro-1H-indole have implemented rigorous quality standards. Current specifications typically require ≥98% purity by HPLC, with strict limits on related substances. Analytical certificates now routinely include chiral purity assessment, reflecting the growing importance of stereochemistry in drug development.

The global market for halogenated indole building blocks like 4-Chloro-6-fluoro-1H-indole is projected to reach $120 million by 2026, driven by pharmaceutical R&D investments. Asia-Pacific regions show particularly strong growth, with several new production facilities coming online to meet demand from contract research organizations and academic institutions.

Recent advances in green chemistry have led to improved synthetic routes for 4-Chloro-6-fluoro-1H-indole. Catalytic methods using recyclable reagents and solvent-free conditions are reducing the environmental impact of production. These sustainable approaches align with the pharmaceutical industry's increasing focus on green chemistry principles throughout the supply chain.

Safety assessments of 4-Chloro-6-fluoro-1H-indole indicate it requires standard laboratory precautions for handling organic compounds. Proper ventilation and personal protective equipment are recommended when working with this material. Material safety data sheets provide detailed guidance on storage conditions and emergency procedures, emphasizing the compound's stability when properly handled.

Looking ahead, researchers anticipate expanding applications for 4-Chloro-6-fluoro-1H-indole in materials science beyond pharmaceuticals. Early studies suggest potential uses in organic electronics and as a ligand in catalytic systems. The compound's unique combination of electronic properties and structural features continues to inspire innovation across multiple scientific disciplines.

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